7-amino-2-(4-methoxyphenyl)tropone | 855399-86-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 7-amino-2-(4-methoxyphenyl)tropone
• 英文别名: 2-amino-7-(4-methoxy-phenyl)-cycloheptatrienone；2-Amino-7-(4-methoxy-phenyl)-cycloheptatrienon；2-Amino-7-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one；2-amino-7-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 855399-86-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: WVQXOUICXIBQMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-amino-2-(4-methoxyphenyl)tropone 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以92%的产率得到α-(4-methoxyphenyl)tropolone
  参考文献：
  名称：

  Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors

  摘要：

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.

  DOI：

  10.1021/ml400158k
• 作为产物：
  描述：

  2-氯-2,4,6-环庚三烯-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 7-amino-2-(4-methoxyphenyl)tropone
  参考文献：
  名称：

  Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors

  摘要：

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.

  DOI：

  10.1021/ml400158k

文献信息

• Nozoe et al., Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1954, vol. <I> 38, p. 141,142
  作者：Nozoe et al.

  DOI：——

  日期：——
• Substituted Tropolone Derivatives and Methods of Use
  申请人：University of Connecticut

  公开号：US20150166448A1

  公开（公告）日：2015-06-18

  The compositions and methods described herein relate generally to substituted tropolone derivatives, which, among other features, are useful as histone deacetylase (HDAC) inhibitors.
• US9790158B2
  申请人：——

  公开号：US9790158B2

  公开（公告）日：2017-10-17
• Nozoe et al., Science Reports of the Tohoku University, Series 1: Physics, Chemistry, Astronomy, 1954, vol. <I> 37, p. 130,134
  作者：Nozoe et al.

  DOI：——

  日期：——
• Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors
  作者：Sophia N. Ononye、Michael D. VanHeyst、E. Zachary Oblak、Wangda Zhou、Mohamed Ammar、Amy C. Anderson、Dennis L. Wright

  DOI：10.1021/ml400158k

  日期：2013.8.8

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.